Process for making morphine-6-glucuronide or substituted morphin

Details Process for making morphine-6-glucuronide or substituted morphin Process for making morphine-6-glucuronide or substituted morphin

1997-04-14

1999-11-02

Robinson, Douglas W.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

536119, 536120, 536124, 546 44, 546 45, 546 46, 514 25, C07G 300, C07H 1524, C07D47100, A61K 3170

Patent

active

059773260

ABSTRACT:
##STR1## Morphine-6-glucuronide or substituted morphine-6-glucuronide of formulae (I) is made by conjugation of a glucuronate ester and/or substituted glucuronate ester with morphine or substituted morphine in the presence of a Lewis acid catalyst and in the absence of silver catalysts and barium hydroxide and other heavy metal derivatives.

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Kaspersen, F.M., and Van Boeckel, C.A.A., "A review of the methods of chemical synthesis of sulphate and glucuronide conjugates", Xenobiotica, vol. 17, No. 12, 1451-1471, Dec. 1987.
Vlahov, J., and Snatzke, G., "Uber eine verbesserte Synthese von .beta.-Glucosiduronsaure-Derivaten", Liebigs Ann. Chem., 1983, 570-574.
Sy, W.-W., et al., "Syntheses of 3-O-and 6-O-Propanoylmorphine--A Reinvestigation and Correction", Journal of Pharmaceutical Sciences, vol. 75, No. 8, Aug. 1986, 787-789.
Saferstein, R., et al, "Chemical Ionization Mass Spectrometry of Morphine Derivatives", Journal of Forensic Sciences, vol. 24, No. 2, Apr. 1979, 312-316.
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Osborne, R., et al., "Analgesic Activity of Morphine-6-Glucuronide", The Lancet, 1988, 828.
Carrupt, P-A., et al., "Morphine-6-Glucuronide and Morphine 3-Glucuronide as Molecular Chameleons with Unexpected Lipophilicity", J. Med. Chem., 1991, 34, 1272-1275.
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